Nitrogen → 2-(5-Chloromethyl-thiophen-2-yl)-2-methyl-[1,3]dioxolane

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-methanol (400 mg, 2.00 mmol) in dry CH2Cl2 (3.7 mL) was treated at 0° C. with Et3N (0.36 mL, 2.60 mmol) followed by DMAP (24 mg, 0.20 mmol) and Ms-Cl (0.19 mL, 2.40 mmol). The reaction mixture was stirred at rt for 2 h before being quenched with water (5 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give crude 2-(5-chloromethyl-thiophen-2-yl)-2-methyl-[1,3]dioxolane as an orange oil. A solution of the crude material in acetone (5.0 mL) was treated, under inert atmosphere (N2) with K2CO3 (829 mg, 6.00 mmol) followed by 5-nitro-1H-pyrazole (226 mg, 2.00 mmol) and TBA bromide (129 mg, 0.40 mmol). The resulting mixture was stirred at rt overnight. Water (15 mL) and EA (20 mL) were added. The aq. layer was extracted with EA (20 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound as a yellow oil. TLC: rf (60:40 hept-EA)=0.24. LC-MS-conditions 02: tR=0.96 min; [M+H]+=296.20.

1. custombefore being quenched with water (5 mL)
2. extractionextracted with CH2Cl2 (10 mL)
3. dry with materialextracts were dried over MgSO4
4. filtrationfiltered
5. customthe solvents were removed under reduced pressure

ORDレコード

ord-fe31cd66e02f4ddf84aec52d81d785e8

出典データセット

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08288419B2